Nitrogen → HCID 90685251, compound

HRID 1944027Notes

Reaction equation

HRID 1944027 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][C@@H:12](OS(C)(=O)=O)[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[N-:26]=[N+:27]=[N-:28].[Na+].CCN(CC)CC.N#N>O.CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[CH2:11][C@H:12]([N:26]=[N+:27]=[N-:28])[CH2:13][CH2:14][C:8]1=[C:7]2[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 33557Sodium AzideHCID 91097697HCID 91097697, compound

Product 1

HCID 90685251HCID 90685251, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
68 °C

Procedure

A reaction mixture of the mesylate of Step 7 (1.67 kg, 4.32 mol), DMF (8.35 L), NaN3 (0.457 kg, 7.03 mol) and Et3N (65 ml, 0.466 mol) under a constant stream of N2 was maintained between 66-70° C. After 18 h, the mixture was cooled to room temperature and H2O (8.45 L) was slowly added with vigorous stirring. The reaction mixture was filtered; the crystals were washed with 1:1 DMF:H2O (16 L), 3:7 DMF:H2O (8.5 L), and water (14 L). The dark brown solid was dried under vacuum and nitrogen.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe crystals were washed with 1:1 DMF
  4. customThe dark brown solid was dried under vacuum and nitrogen

Sources & evidence

ORD record
ord-329d873c98374fc29f8f1de7c9d57973
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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